EP0772602A2 - Procede de preparation d'imidazolidinones disubstituees en 1,3 - Google Patents

Procede de preparation d'imidazolidinones disubstituees en 1,3

Info

Publication number
EP0772602A2
EP0772602A2 EP95926920A EP95926920A EP0772602A2 EP 0772602 A2 EP0772602 A2 EP 0772602A2 EP 95926920 A EP95926920 A EP 95926920A EP 95926920 A EP95926920 A EP 95926920A EP 0772602 A2 EP0772602 A2 EP 0772602A2
Authority
EP
European Patent Office
Prior art keywords
radicals
imidazolidin
dioxalan
reaction
disubstituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP95926920A
Other languages
German (de)
English (en)
Other versions
EP0772602B1 (fr
Inventor
Jochem Henkelmann
Thomas RÜHL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0772602A2 publication Critical patent/EP0772602A2/fr
Application granted granted Critical
Publication of EP0772602B1 publication Critical patent/EP0772602B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom

Definitions

  • the present invention relates to the preparation of 1,3-disubstituted imidazolidin-2-ones, from 1,3-dioxalan-2-one (ethylene carbonate) and primary amines.
  • 1,3-disubstituted imidazolidin-2-ones are interesting polar, non-protic solvents, in particular for high-molecular compounds such as polyamides, polyvinyl chloride, polyvinyl alcohol, polystyrene, polyurethane and phenolic resins . Furthermore, 1,3-disubstituted imidazolidin-2-ones are used as finishing agents in the textile industry.
  • N, N'-disubstituted diamines with urea (EP 198 345), which must be carried out in solvent, or with the toxicologically questionable phos gene (EP 183 076) are also known. Also described are the syntheses from carbon dioxide, primary amine and ethylene glycol (JP 5 9155-364-A) or dichloroethane and the Leukart-Wallach reaction for the synthesis of 1,3-dimethylimidazolidinone, which requires a heterogeneous hydrogenation catalyst (GB 1517820 ; DE 1545614; US 2,422,400). The object of the invention was to develop a synthetic route for 1,3-disubstituted imidazolidin-2-ones which is simple and economical. In particular, the method is said to be superior to known synthetic routes from an environmental point of view.
  • radicals R which may be the same or different, a) hydrogen; b) straight-chain, branched or cyclic alkyl radicals with 1 to 12 C atoms, which in turn contain C 6 . 10 aryl, Fl, Cl, Br can be substituted; c) aryl residues with 6 to 10 carbon atoms, which in turn can be substituted with C ⁇ - alkyl; d) heteroalkyl radicals in which the alkyl radicals as defined above are interrupted by one or more heteroatoms selected from O, S and N, e) heteroaryl radicals having 5 to 10 ring atoms and containing 1 to 3 heteroatoms selected from O, S, N,
  • a preferred process product is 1,3-dimethylimidazolidin-2-one.
  • the reaction is generally carried out at 150 ° C. to 300 ° C., preferably at 200 ° C. to 250 ° C., particularly preferably under autogenous pressure.
  • the intrinsic pressure that is established is usually between 50 and 150 bar.
  • the amount of primary amine used with respect to ethylene carbonate is advantageously stoichiometric or superstoichiometric, e.g. 5 times stoichiometric, preferably in the range of a 1.5 to 3 times stoichiometric excess.
  • reaction time of up to about 24 hours has often proven to be sufficient.
  • the yield of the process can generally be increased using water.
  • the amount of water used can be up to 50% by weight. advantageously 30 to 45% by weight, based on the ethylene carbonate used. be.
  • the reaction mixture can be worked up by simple distillation of the raw product.
  • Example 2 The same batch as in Example 1 was heated at 250 ° C. for 24 hours without water. The subsequent work-up gave 476 g of 1,3-dimethyl-imidazolidin-2-one (75% yield).
  • Example 5 Ethylene carbonate and methylamine were reacted and worked up as in Example 3, but at 200 ° C. The yield was 42%.
  • Example 5 Ethylene carbonate and methylamine were reacted and worked up as in Example 3, but at 200 ° C. The yield was 42%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Afin de préparer des imidazolidin-2-ones, on fait réagir 1,3-dioxalan-2-one (carbonate d'éthylène) avec au moins un composé ayant la formule RNH2, dans laquelle R peut désigner entre autres H, alcoyle, aryle, hétéroalcoyle ou hétéroaryle.
EP95926920A 1994-07-20 1995-07-18 Procede de preparation d'imidazolidinones disubstituees en 1,3 Expired - Lifetime EP0772602B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4425696 1994-07-20
DE4425696A DE4425696A1 (de) 1994-07-20 1994-07-20 Verfahren zur Herstellung 1,3-disubstituierter Imidazolidinone
PCT/EP1995/002806 WO1996002516A2 (fr) 1994-07-20 1995-07-18 Procede de preparation d'imidazolidinones disubstituees en 1,3

Publications (2)

Publication Number Publication Date
EP0772602A2 true EP0772602A2 (fr) 1997-05-14
EP0772602B1 EP0772602B1 (fr) 2000-09-20

Family

ID=6523692

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95926920A Expired - Lifetime EP0772602B1 (fr) 1994-07-20 1995-07-18 Procede de preparation d'imidazolidinones disubstituees en 1,3

Country Status (7)

Country Link
US (1) US5783706A (fr)
EP (1) EP0772602B1 (fr)
JP (1) JPH10502917A (fr)
AU (1) AU3113195A (fr)
DE (2) DE4425696A1 (fr)
ES (1) ES2151077T3 (fr)
WO (1) WO1996002516A2 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19743760A1 (de) * 1997-10-02 1999-04-08 Basf Ag Verfahren zur Herstellung von cyclischen Harnstoffderivaten
DE19822678A1 (de) * 1998-05-20 1999-11-25 Bayer Ag Substituierte 1,3-Diaza-2-(thi)oxo-cycloalkane
ES2209497T3 (es) * 1998-09-11 2004-06-16 Ciba Specialty Chemicals Holding Inc. Composicion polimerica de mejores caracteristicas de brillo.
EP0992497B1 (fr) * 1998-10-09 2003-12-17 Mitsui Chemicals, Inc. Procédé de préparation des Dérivés de 1,3-dialkyl-2-imidazolinones
JP4541468B2 (ja) * 1998-10-09 2010-09-08 三井化学株式会社 １，３−ジアルキル−２−イミダゾリジノン類及びその製造方法
DE60143350D1 (de) * 2001-01-04 2010-12-09 Mitsui Chemicals Inc Verfahren zur herstellung von 1,3-dialkyl-2-imidazolidinon-derivaten
US7238164B2 (en) 2002-07-19 2007-07-03 Baxter International Inc. Systems, methods and apparatuses for pumping cassette-based therapies
CN111410633B (zh) * 2020-03-30 2021-08-20 迈奇化学股份有限公司 一种1,3-二甲基-2-咪唑啉酮的连续生产方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422400A (en) * 1944-04-07 1947-06-17 Du Pont Production of n-methylamides
US2892843A (en) * 1958-04-30 1959-06-30 Dow Chemical Co Preparation of ethylene urea
BE685921A (fr) * 1965-08-25 1967-02-24
DE1545614C3 (de) * 1965-08-27 1974-08-29 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von 2-Oxo-hexahydropyrimidinen
IT1051036B (it) * 1975-12-03 1981-04-21 Snam Progetti Procedimento per la sintesi di n metil uree
JPS59155364A (ja) * 1983-02-24 1984-09-04 Nissan Chem Ind Ltd １，３−ジメチル−２−イミダゾリジノンの製造方法
CA1259321A (fr) * 1984-11-01 1989-09-12 Nobuyuki Kajimoto Procede de production de 1,3-dimethyl-2- imidazolidinone
US4731453A (en) * 1985-04-03 1988-03-15 Mitsui Toatsu Chemicals, Inc. Process for producing 1, 3-dialkyl-2-imidazolidinone
US4617400A (en) * 1985-09-11 1986-10-14 Kawaken Fine Chemicals Co., Ltd. Process for preparing cyclic urea derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9602516A2 *

Also Published As

Publication number Publication date
WO1996002516A2 (fr) 1996-02-01
US5783706A (en) 1998-07-21
DE4425696A1 (de) 1996-01-25
ES2151077T3 (es) 2000-12-16
AU3113195A (en) 1996-02-16
JPH10502917A (ja) 1998-03-17
EP0772602B1 (fr) 2000-09-20
DE59508742D1 (de) 2000-10-26
WO1996002516A3 (fr) 1996-04-25

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